codeine-6-glucuronide
Sign in to saveAlso known as Morphinan, 7,8-didehydro-4,5a-epoxy-6a-(b-D-glucopyranuronosyloxy)-3-methoxy-17-methyl- (8CI), C16577, Codeine glucuronide, Glucopyranosiduronicacid, 7,8-didehydro-4,5a-epoxy-3-methoxy-17-methylmorphinan-6a-yl, b-D- (8CI), Glucopyranosiduronic acid, codeine, b-D- (6CI)
Codeine-6-glucuronide (C6G) is a major active metabolite of codeine and may be responsible for as much as 60% of the analgesic effects of codeine. C6G exhibits decreased immunosuppressive effects compared to codeine. During its metabolism, codeine is conjugated with glucuronic acid by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7) to form codeine-6-glucuronide.
Wikidata facts
- Mass
- 475.184232
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- chemical formula
- C₂₄H₂₉NO₉
- canonical SMILES
- CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)OC6C(C(C(C(O6)C(=O)O)O)O)O
- isomeric SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O
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{{Chembox | ImageFile = Codeine-6-glucuronide.svg | ImageClass = skin-invert-image | ImageSize = 200px | IUPACName = (5α,6α)-3-methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-yl β-D-glucopyranosiduronic acid | PIN = (2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-yl]oxy}oxane-2-carboxylic acid | OtherNames = |Section1= |Section2= |Section3= }}
Codeine-6-glucuronide (C6G) is a major active metabolite of codeine and may be responsible for as much as 60% of the analgesic effects of codeine. C6G exhibits decreased immunosuppressive effects compared to codeine. During its metabolism, codeine is conjugated with glucuronic acid by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7) to form codeine-6-glucuronide.